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DOI | 10.1126/science.aan0003 |
A modular and enantioselective synthesis of the pleuromutilin antibiotics | |
Murphy, Stephen K.1; Zeng, Mingshuo1; Herzon, Seth B.1,2 | |
2017-06-02 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2017 |
卷号 | 356期号:6341页码:956-959 |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | The tricyclic diterpene fungal metabolite (+)-pleuromutilin has served as a starting point for antibiotic development. Semisynthetic modification of its glycolic acid subunit at C14 provided the first analogs fit for human use, and derivatization at C12 led to 12-epi-pleuromutilins with extended-spectrum antibacterial activity, including activity against Gram-negative pathogens. Given the inherent limitations of semisynthesis, however, accessing derivatives of (+)-pleuromutilin with full control over their structure presents an opportunity to develop derivatives with improved antibacterial activities. Here we disclose a modular synthesis of pleuromutilins by the convergent union of an enimide with a bifunctional iodoether. We illustrate our approach through synthesis of (+)-12-epimutilin, (+)-11,12-di-epi-mutilin, (+)-12-epi-pleuromutilin, (+)-11,12-di-epi-pleuromutilin, and (+)-pleuromutilin itself in 17 to 20 steps. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000402552300035 |
WOS关键词 | (+)-PLEUROMUTILIN ; DISCOVERY ; (+/-)-PLEUROMUTILIN ; CHEMISTRY ; SUBUNIT ; CARBON |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/196170 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Yale Univ, Dept Chem, 225 Prospect St, New Haven, CT 06520 USA; 2.Yale Sch Med, Dept Pharmacol, New Haven, CT 06520 USA |
推荐引用方式 GB/T 7714 | Murphy, Stephen K.,Zeng, Mingshuo,Herzon, Seth B.. A modular and enantioselective synthesis of the pleuromutilin antibiotics[J]. SCIENCE,2017,356(6341):956-959. |
APA | Murphy, Stephen K.,Zeng, Mingshuo,&Herzon, Seth B..(2017).A modular and enantioselective synthesis of the pleuromutilin antibiotics.SCIENCE,356(6341),956-959. |
MLA | Murphy, Stephen K.,et al."A modular and enantioselective synthesis of the pleuromutilin antibiotics".SCIENCE 356.6341(2017):956-959. |
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